HCID 67003585, compound → HCID 67003633, compound

Participants

Reaction Steps

A solution of 5-chloro-4-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Example 1D) (7.12 g, 16.46 mmol), bis(triphenylphosphine)palladium dichloride (0.809 g, 1.15 mmol), and 2-(1-(methoxymethoxy)cyclobutyl)-5-(tributylstannyl)thiazole (Example 1C) (10.45 g, 21.39 mmol) in N,N-dimethylformamide (54.9 ml) was heated to 70° C. for 1 hour. The reaction was cooled to room temperature and quenched by the addition of an aqueous potassium fluoride solution (19 g in 100 mL water) and ethyl acetate (200 mL). The mixture was stirred vigorously overnight and was then filtered through diatomaceous earth, eluting with ethyl acetate. The layers were separated, and the organic layer was washed with aqueous saturated bicarbonate solution and water. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 35% ethyl acetate in hexane, to afford the title compound. MS ESI(+) m/z 504 [M+H]+.

Provenance & Evidence